EP2273987B1 - Préparation en forme de film comprenant des substances huileuses et destinée à l'administration orale - Google Patents
Préparation en forme de film comprenant des substances huileuses et destinée à l'administration orale Download PDFInfo
- Publication number
- EP2273987B1 EP2273987B1 EP09745504.2A EP09745504A EP2273987B1 EP 2273987 B1 EP2273987 B1 EP 2273987B1 EP 09745504 A EP09745504 A EP 09745504A EP 2273987 B1 EP2273987 B1 EP 2273987B1
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- European Patent Office
- Prior art keywords
- weight
- preparation
- preparation according
- film
- oily substance
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7007—Drug-containing films, membranes or sheets
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
Definitions
- the present invention relates to solid, film-like preparations with at least one oily substance for oral administration as defined in claim 1.
- the U.S. Patent No. 4,128,445 discloses technical solutions in the loading of carrier material with active ingredients and is based on the subsequent addition of active compound preparations on prefabricated sheet-like preparations. It describes loading processes in dry and moist form, the aim of a uniform, subsequent distribution of active ingredient on a layer.
- the US2004 / 137027 A1 discloses film preparations for oral administration containing 0.5 to 30% of flavorings such as essential oils in a matrix of at least 40% polyvinyl alcohol.
- a formulation suitable for the preparation of film-like flavor-containing preparations is disclosed in US Pat EP 0 460 588 described. Particular advantages are seen in the composition of 20 to 60 wt .-% film former, 2 to 40 wt .-% gelling agent, 0.1 to 35 wt .-% active or flavoring agent and a maximum of 40 wt .-% of an inert filler.
- Gel former among other compounds, is called polyvinyl alcohol. It turns out, however, that the gel-forming properties of polyvinyl alcohol are only partially compatible with the film formers mentioned in this document.
- Aroma-containing sheet-like dosage forms for use in the mouth are also from the EP 0 452 446 However, no measures are described how a flavor evaporation can be prevented during production and / or storage.
- sheet-like dosage forms that disintegrate rapidly on contact with liquid and can be produced while avoiding drug losses in their preparation and storage.
- These film-shaped administration forms have an inner, fat-soluble phase in the form of droplets in which the flavoring agent is present and which are distributed in an outer, solid, but water-soluble phase, wherein the outer phase, based on the anhydrous portions, at least 40 wt. % Polyvinyl alcohol, up to 30% by weight a surfactant and 0.1 to 30% by weight of inner phase, based on the outer phase.
- Film-form preparations for use in the mouth are already commercially available as active substance-containing or flavoring-containing dosage forms.
- wafer-thin strips that leave a cool, breath-fresh taste sensation on the tongue without sucking or chewing, in the flavors "Peppermint”, “Wild-Mint” and “Lemon-Frost” by Wrigley under the name ECLIPSE FLASH TM or by Pfizer in the flavors "Cool Mint ® ", “FreshBurst ® ", Cinnamon and "Fresh Citrus” under the brand name Listerine PocketPaks ® offered.
- Hydrophilic film-forming polymers are used for the rapid disintegration or rapid dissolution of film-like formulations upon contact with saliva.
- hydrophilic polymers usually have only a low absorption capacity for lipophilic substances, the amount of oily substance with which hydrophilic films can be loaded is limited. This limitation becomes particularly clear when larger amounts of an oily liquid with a hydrophilic polymer are processed into a film, because this leads to a sweating of the oily substance, for example, through Phase separation during mass production (separation of the O / W emulsion) or later during storage of the films.
- a large amount of oily substance in a film-like preparation For certain applications, however, it is necessary to accommodate a large amount of oily substance in a film-like preparation. For example, to achieve desired therapeutic effects, it may be necessary to load the film with a large amount of an oily drug.
- an oily drug For example, for the active ingredient simethicone, which is used as a carminative, a dose of about 80 mg is indicated to be therapeutically effective. This amount is administered for example by means of known liquid dosage form. However, for administration by means of a rapidly disintegrating film-like preparation in the mouth, this amount would be too large to produce stable films.
- the film-forming polymers which are able to stabilize larger amounts of at least one oily substance even without the addition of further surface-active substances, are fully hydrolyzed polyvinyl alcohols and partially hydrolyzed polyvinyl alcohols.
- Polyvinyl alcohols are water-soluble polymers of vinyl alcohol.
- Vinyl alcohol is usually present in the tautomeric form of the acetaldehyde. Therefore, polyvinyl alcohol can not be produced by polymerization of its monomers, but is obtained by saponification of polyvinyl acetate.
- polyvinyl acetate is hydrolyzed or hydrolyzed with sodium hydroxide.
- the polyvinyl alcohols that have not been completely saponified with sodium hydroxide contain vinyl alcohol and vinyl acetate units. These polyvinyl alcohols are referred to as partially hydrolyzed polyvinyl alcohols.
- the water-soluble, solid, film-like preparations according to the invention comprise from 30 to 80% by weight, preferably from 40 to 60% by weight, of at least one oily substance and from 5 to 70% by weight, in the preferred embodiment from 5 to 60% by weight. , at least one partially hydrolyzed or fully hydrolyzed polyvinyl alcohol.
- the water-soluble, film-shaped preparation comprises partially hydrolyzed polyvinyl alcohols, in particular partially hydrolyzed polyvinyl alcohols having a degree of hydrolysis of about 88%, that is to say having a degree of hydrolysis of from 86.7 to 88.7%.
- the teilhydrolys faced polyvinyl alcohols have a degree of hydrolysis of about 88%, and a viscosity between 4 and 40 mPa ⁇ s as a 4% aqueous solution at 20 ° C.
- polyvinyl alcohols available under the trade name Mowiol ® from Kuraray Specialties Europe GmbH Mowiol ® 5-88, Mowiol ® 8-88, Mowiol ® 13-88, Mowiol ® 18-88, Mowiol ® 23 -88, Mowiol ® 26-88 and Mowiol ® 32-88 and similar products are called.
- Oily substances are understood to mean, at room temperature (20 ° C. to 23 ° C.) and liquid substances which are difficult or insoluble in water, mixtures of such substances and those substances with constituents dissolved therein.
- the oily substances according to claim 1 include compounds such as mineral oils (hydrocarbons obtained mainly by distillation and refining from petroleum), synthetic oils, synthetic oils which are esters of dicarboxylic acids, and silicone oils.
- mineral oils hydrocarbons obtained mainly by distillation and refining from petroleum
- synthetic oils synthetic oils which are esters of dicarboxylic acids
- silicone oils silicone oils
- at least one oily substance from the group of fatty oils and essential oils may be present.
- the oily substances may be pharmaceutically active substances such as dimethicone or simethicone, but the oily substances may also have other functions, for example as a flavoring agent.
- the oily substance is dimethicone or simethicone.
- Dimethicone chemically ⁇ (trimethylsilyl) - ⁇ -methylpoly [oxy (dimethylsilylene)]
- Simethicone is silica blended dimethicone. Both are drugs that are used orally as an antifoaming agent to relieve bloating and pain caused by too much gas in the gastrointestinal tract.
- Simethicone is available as a chewable tablet or in liquid form as a medicine. Preparations name for the commercially available drugs, for example, Elugan ®, Endo-Paractol ®, Espumisan ®, Imogas ®, Lefax ® and simethicone-ratiopharm ®.
- oily substances that may be included in the formulation are menthol, bitter fennel oil, peppermint oil, caraway oil.
- Peppermint oil (Menthae piperitae aetheroleum) is an essential oil derived from peppermint (Mentha piperita ). Peppermint oil is used as a carminative and, because of its digestive and exfoliating properties, is used to treat spasms in the upper gastrointestinal tract and biliary tract.
- the main constituent of peppermint oil is menthol and menthone.
- Menthol is a monocyclic monoterpene alcohol that is poorly soluble in water at 0.4 g / l. At room temperature, menthol is a colorless, crystalline solid.
- Caraway oil (Carvi aetheroleum) is an essential oil derived from the fully ripe fruits of the caraway plant ( Carum carvi L.). It is also used as a carminative.
- Bitter fennel oil is an essential oil from the German fennel (Foeniculi amari fructus), which is obtained by steam distillation from the seeds.
- Bitterfat oil has a digestive and antispasmodic effect on the stomach and intestines.
- the preparation according to the invention may consist of from 5 to 70% by weight of at least one partially or fully hydrolyzed polyvinyl alcohol of from 30 to 80% by weight of at least one oily substance.
- the film-shaped preparation according to the invention based on the dry fraction, consists of 40% by weight of at least one partially or fully hydrolyzed polyvinyl alcohol and 60% by weight of at least one oily substance, preferably dimethicone or simethicone.
- the preparation contains, in addition to dimethicone or simethicone, at least one essential oil from the group comprising peppermint oil, bitter fennel oil and caraway oil.
- the invention is not limited to water-soluble, solid, film-like preparations of at least one polyvinyl alcohol and one or more oily substances.
- the film-like preparation may contain further hydrophilic polymers, even if these films can not be used to produce stable films with an oily substance in large quantities, if only these polymers are used as matrix material and no further surface-active substances are added.
- the additional hydrophilic polymers are selected from the group consisting of cellulose and cellulose derivatives, polyvinylpyrrolidones, polyethylene oxides, pullulan, hydroxypropylated tapioca starch and alginates.
- the additional hydrophilic polymers are selected from the group consisting of hydroxypropylmethylcellulose and sodium carboxymethylcellulose.
- the film-like preparations may contain other auxiliaries or additives.
- the polymer composition for the preparation of the film-shaped preparation Glycerol, sorbidex, sucralose, menthol and / or dyes are added.
- Table 1 Quantities of the components contained in the preparation component proportion of Polyvinyl alcohol (fully / partially hydrolyzed) 5-70% by weight Oily component 30-80% by weight hydroxypropyl methylcellulose 0-35% by weight Natriumcarbocymethylcellulose 0-35% by weight glycerin 0-20% by weight Sorbidex 0-20% by weight sucralose 0-2% by weight menthol 0-10% by weight Bitter fennel oil 0-5% by weight peppermint oil 0-5% by weight cumin 0-5% by weight total 100% by weight
- compositions of the invention can be prepared by a composition comprising at least one film-forming polymer from the group of fully and partially hydrolyzed polyvinyl alcohols and at least 30 wt .-%, based on the Dry portion of the preparation, a water-insoluble, oily liquid in an aqueous solvent, preferably water, is produced. With this mass then a pad is coated and dried the resulting coating.
- the film-like preparations containing as an oily substance dimethicone, simethicone, peppermint oil, bitter fennel oil and / or caraway oil can be used as a carminative, because they can treat complaints in the gastrointestinal tract, such as bloating, convulsions and / or flatulence and alleviated.
- a homogeneous composition of the following composition was prepared: 16% by weight Polyvinyl alcohol (Mowiol ® 8-88, partially hydrolyzed polyvinyl alcohol, degree of hydrolysis: 85-89%, viscosity (4% in H 2 O, 20 ° C): 7 - 9 mPa ⁇ s) 24% by weight simethicone 60% by weight water
- a homogeneous composition of the following composition was prepared: 14% by weight Sodium carboxymethyl cellulose (Walocel CRT ® 30 GA; DS: 0.65 to 1.45, viscosity (2%): 20 - 40 mPa ⁇ s) 6% by weight simethicone 80% by weight water
- a homogeneous composition of the following composition was prepared: 21% by weight Polyvinylpyrrolidone (Kollidon ® 90; K value: 81.0 to 96.3)) 9% by weight simethicone 70% by weight water
- a homogeneous composition of the following composition was prepared: 17.5% by weight Polyethylene oxide (Polyox ® WSR N80; viscosity (5%, 25 ° C): 55 to 90 cP) 7.5% by weight simethicone 75.0% by weight water
- a homogeneous composition of the following composition was prepared: 28% by weight Pullulan (PI-20; viscosity: 128 mm 2 / s) 12% by weight simethicone 60% by weight water
- a homogeneous composition of the following composition was prepared: 4.4% by weight Sodium alginate (Manucol ® LDP MCLLDP 25BG; viscosity (1%): 4.00 to 15.00) 6.6% by weight simethicone 89.0% by weight water
- a homogeneous composition of the following composition was prepared: 10.4% by weight Hydroxypropyl cellulose (Klucel LF ®; viscosity (5%): 75-150 mPa ⁇ s) 15.6% by weight simethicone 74.0% by weight water
- Example recipe for a stable film with simethicone 27.48% by weight Mowiol 8-88 58.00% by weight simethicone 10.00% by weight Minty 1.00% by weight sucralose 2.50% by weight Sorbidex 1.00% by weight Titanium dioxide 0.02% by weight Patent Blue
- Example recipe for a stable film with simethicone 26.09% by weight Mowiol 8-88 7.00% by weight
- Pharmacoat 606 hydroxypropylmethylcellulose, substitution type 2910, viscosity (2% by weight in H 2 O): 4.8 - 7.2 mPa ⁇ s) 0.50% by weight Walocel CRT 30 GA 57.14% by weight simethicone 3.00% by weight glycerin 3.00% by weight Sorbidex 0.35% by weight sucralose 0.40% by weight menthol 1.00% by weight Bitter fennel oil 1.00% by weight peppermint oil 0.50% by weight cumin 0.02% by weight Yellow No. 6
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
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- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (16)
- Préparation en forme de film, solide, soluble dans l'eau et destinée à l'administration orale, comprenant au moins un polymère filmogène du groupe des alcools polyvinyliques complètement ou partiellement hydrolysés et au moins une substance huileuse, qui est incorporée dans le polymère filmogène et dont la proportion vaut au moins 30 % en poids, rapportée à la proportion à sec de la préparation, dans laquelle la préparation contient au moins une substance huileuse sélectionnée dans le groupe composé d'huiles minérales et d'huiles synthétiques, qui sont des esters d'acides dicarboxyliques, et d'huiles de silicone, ainsi que, au choix en plus, au moins une substance huileuse sélectionnée dans le groupe des huiles grasses et des huiles essentielles.
- Préparation selon la revendication 1, caractérisée en ce que l'alcool polyvinylique partiellement hydrolysé est sélectionné dans le groupe des alcools polyvinyliques partiellement hydrolysés, qui présentent un degré d'hydrolyse d'environ 88 %.
- Préparation selon la revendication 1 ou 2, caractérisée en ce que le polyalcool polyvinylique partiellement hydrolysé présente, comme solution aqueuse à 4 %, une viscosité de 4 à 40 mPa.s à 20°C.
- Préparation selon la revendication 1, caractérisée en ce que la substance huileuse est sélectionnée dans le groupe qui se compose de la siméthicone et du diméthicone.
- Préparation selon l'une quelconque des revendications précédentes, caractérisée en ce que la proportion de la substance huileuse vaut au moins 40 % en poids, de préférence au moins 50 % en poids, rapportée à la proportion à sec de la préparation.
- Préparation selon l'une quelconque des revendications précédentes, caractérisée en ce que la proportion de la substance huileuse vaut au maximum 80 % en poids, de préférence au maximum 60 % en poids, rapportée à la proportion à sec de la préparation.
- Préparation selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle contient au moins une substance huileuse du groupe composé de l'huile essentielle d'aneth, l'huile essentielle de menthe poivrée et l'huile essentielle de carvi.
- Préparation selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle comprend au moins un autre polymère hydrophile.
- Préparation selon la revendication 8, caractérisée en ce que l'autre polymère est sélectionné dans le groupe, qui comprend des celluloses, des dérivés de cellulose, la polyvinylpyrrolidone, des oxydes de polyéthylène, le pullulane, l'amidon de tapioca hydroxypropylé et des alginates.
- Préparation selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle comprend une ou plusieurs substances d'addition, de préférence du groupe qui comprend la glycérine, le sorbidex, le sucralose, le menthol et des colorants.
- Préparation selon la revendication 1, caractérisée en ce qu'elle présente une composition selon le tableau suivant:
Composant Proportion Alcool polyvinylique complètement/partiellement hydrolysé) 5 - 70 % en poids Composant huileux, comme défini dans la revendication 1 30 - 80 % en poids Hydroxypropylméthylcellulose 0 - 35 % en poids Carboxyméthylcellulose de sodium 0 - 35 % en poids Glycérine 0 - 20 % en poids Sorbidex 0 - 20 % en poids Sucralose 0 - 2 % en poids Menthol 0 - 10 % en poids Huile essentielle d'aneth 0 - 5 % en poids Huile essentielle de menthe poivrée 0 - 5 % en poids Huile essentielle de carvi 0 - 5 % en poids Total 100 % en poids - Préparation selon la revendication 11, caractérisée en ce qu'elle ne contient pas de substances tensioactives.
- Procédé de production d'une préparation selon l'une quelconque des revendications précédentes, caractérisé en ce que l'on revêt un support, dans un agent solvant aqueux, avec une masse comprenant au moins un alcool polyvinylique complètement ou partiellement hydrolysé et au moins 30 % en poids, rapportés à la proportion à sec de la préparation, d'une substance huileuse, telle qu'elle est définie dans la revendication 1, et on sèche le revêtement.
- Procédé selon la revendication 13, caractérisé en ce que l'agent solvant est l'eau.
- Procédé selon la revendication 13 ou 14, caractérisé en ce que l'on effectue la production sans ajout de substances tensioactives.
- Préparation selon l'une quelconque des revendications 1 à 12 à utiliser comme carminatif pour le traitement des douleurs du tractus gastro-intestinal.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008023345.5A DE102008023345B4 (de) | 2008-05-13 | 2008-05-13 | Filmförmige Zubereitung mit öligen Substanzen zur oralen Verabreichung |
PCT/EP2009/003138 WO2009138170A2 (fr) | 2008-05-13 | 2009-04-30 | Préparation en forme de film comprenant des substances huileuses et destinée à l'administration orale |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2273987A2 EP2273987A2 (fr) | 2011-01-19 |
EP2273987B1 true EP2273987B1 (fr) | 2013-07-31 |
Family
ID=40863404
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09745504.2A Active EP2273987B1 (fr) | 2008-05-13 | 2009-04-30 | Préparation en forme de film comprenant des substances huileuses et destinée à l'administration orale |
Country Status (13)
Country | Link |
---|---|
US (1) | US8758803B2 (fr) |
EP (1) | EP2273987B1 (fr) |
JP (1) | JP5654451B2 (fr) |
KR (1) | KR101588479B1 (fr) |
CN (1) | CN102026630B (fr) |
AU (1) | AU2009248328C1 (fr) |
BR (1) | BRPI0907298B8 (fr) |
CA (1) | CA2724191C (fr) |
DE (1) | DE102008023345B4 (fr) |
ES (1) | ES2426963T3 (fr) |
MX (1) | MX2010011923A (fr) |
WO (1) | WO2009138170A2 (fr) |
ZA (1) | ZA201007107B (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9532952B2 (en) | 2011-01-28 | 2017-01-03 | Physician's Seal, LLC | Controlled-release compositions of melatonin combined with sedative and/or analgesic ingredients |
WO2012103411A2 (fr) | 2011-01-28 | 2012-08-02 | Zx Pharma, Llc | Composition de mélatonine à libération contrôlée et procédés associés |
US8808736B2 (en) | 2011-02-11 | 2014-08-19 | Zx Pharma, Llc | Enteric coated multiparticulate controlled release peppermint oil composition and related methods |
CN103442727B (zh) | 2011-02-11 | 2016-08-10 | Zx制药有限责任公司 | 多微粒l-薄荷醇制剂及相关方法 |
US8911780B2 (en) | 2011-02-11 | 2014-12-16 | Zx Pharma, Llc | Multiparticulate L-menthol formulations and related methods |
DE202011004425U1 (de) * | 2011-03-25 | 2012-03-27 | Maria Clementine Martin Klosterfrau Vertriebsgesellschaft Mbh | Zusammensetzung zur Anwendung bei Verdauungsbeschwerden |
RS58325B1 (sr) | 2013-04-23 | 2019-03-29 | Zx Pharma Llc | Enterosolventno obloženi višečestični preparat sa proteinskom sub-oblogom |
WO2016015813A1 (fr) * | 2014-07-30 | 2016-02-04 | Merck Patent Gmbh | Composition apte à la compression directe et contenant de la cellulose microcristalline |
EP3174530B1 (fr) | 2014-07-30 | 2018-08-29 | Merck Patent GmbH | Polyalcools de vinyle aptes à la compression directe |
CA3155406A1 (fr) | 2019-11-04 | 2021-05-14 | Meir Haber | Films administrables par voie orale comprenant des principes actifs peu solubles dans l'eau et leur preparation |
CN111939332B (zh) * | 2020-08-25 | 2022-07-05 | 深圳市泓云润泽医疗科技有限公司 | 一种在消化道中可溶解的医用材料及其应用 |
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US5001A (en) * | 1847-03-06 | Horse-power | ||
GB1142325A (en) | 1965-05-14 | 1969-02-05 | Higham Stanley Russell | Means for administering drugs |
DE2449865B2 (de) | 1974-10-17 | 1981-06-19 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Folienförmiges Arzneimittel |
AU514195B2 (en) | 1975-12-15 | 1981-01-29 | F. Hoffmann-La Roche & Co. | Dosage form |
US4849246A (en) | 1985-10-09 | 1989-07-18 | Wolfgang Schmidt | Process for producing an administration or dosage form for drugs, reagents or other active ingredients |
BR9006965A (pt) | 1989-10-14 | 1991-11-12 | Desitin Arzneimittel Gmbh | Agentes de higiene dental e oral |
DE4018247A1 (de) | 1990-06-07 | 1991-12-12 | Lohmann Therapie Syst Lts | Herstellungsverfahren fuer schnellzerfallende folienfoermige darreichungsformen |
US5192802A (en) * | 1991-09-25 | 1993-03-09 | Mcneil-Ppc, Inc. | Bioadhesive pharmaceutical carrier |
DE19646392A1 (de) | 1996-11-11 | 1998-05-14 | Lohmann Therapie Syst Lts | Zubereitung zur Anwendung in der Mundhöhle mit einer an der Schleimhaut haftklebenden, Pharmazeutika oder Kosmetika zur dosierten Abgabe enthaltenden Schicht |
DE19652257A1 (de) * | 1996-12-16 | 1998-06-18 | Lohmann Therapie Syst Lts | Einzeln dosierte, bei Kontakt mit Flüssigkeit schnell zerfallende, wirkstoff- und insbesondere aromastoffhaltige, folienförmige Darreichnungsform |
US7083781B2 (en) * | 1999-08-19 | 2006-08-01 | Lavipharm S.A. | Film forming polymers, methods of use, and devices and applications thereof |
US20050019291A1 (en) | 2003-07-24 | 2005-01-27 | Yelena Zolotarsky | Emulsion composition of polyvinyl alcohol which forms a peelable film on skin |
CA2593492C (fr) * | 2005-01-19 | 2011-12-13 | Neurohealing Pharmaceuticals, Inc. | Methodes et compositions permettant de reduire la production de salive |
DE102006003512A1 (de) * | 2006-01-24 | 2007-08-02 | Bayer Schering Pharma Ag | Plättchenförmige Arzneimittel zur transbukkalen Applikation von Arzneistoffen |
EP2120895A2 (fr) * | 2007-01-12 | 2009-11-25 | MonoSol Rx LLC | Compositions de films à dose élevée et procédés de préparation |
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2008
- 2008-05-13 DE DE102008023345.5A patent/DE102008023345B4/de not_active Expired - Fee Related
-
2009
- 2009-04-30 EP EP09745504.2A patent/EP2273987B1/fr active Active
- 2009-04-30 WO PCT/EP2009/003138 patent/WO2009138170A2/fr active Application Filing
- 2009-04-30 ES ES09745504T patent/ES2426963T3/es active Active
- 2009-04-30 CA CA2724191A patent/CA2724191C/fr not_active Expired - Fee Related
- 2009-04-30 US US12/736,521 patent/US8758803B2/en active Active
- 2009-04-30 MX MX2010011923A patent/MX2010011923A/es active IP Right Grant
- 2009-04-30 CN CN200980116814.9A patent/CN102026630B/zh not_active Expired - Fee Related
- 2009-04-30 BR BRPI0907298A patent/BRPI0907298B8/pt not_active IP Right Cessation
- 2009-04-30 KR KR1020107027980A patent/KR101588479B1/ko active IP Right Grant
- 2009-04-30 JP JP2011508812A patent/JP5654451B2/ja not_active Expired - Fee Related
- 2009-04-30 AU AU2009248328A patent/AU2009248328C1/en not_active Ceased
-
2010
- 2010-10-06 ZA ZA2010/07107A patent/ZA201007107B/en unknown
Non-Patent Citations (1)
Title |
---|
JÜRGEN FALBE, ELISABETH HILLEN-MASKE: "Römpp Chemie Lexikon", GEORG THIEME VERLAG, STUTTGART, article MINERALÖLE, pages: 2799, 9 * |
Also Published As
Publication number | Publication date |
---|---|
JP5654451B2 (ja) | 2015-01-14 |
WO2009138170A2 (fr) | 2009-11-19 |
CA2724191C (fr) | 2016-05-24 |
CN102026630B (zh) | 2015-11-25 |
BRPI0907298A2 (pt) | 2016-07-05 |
MX2010011923A (es) | 2010-11-30 |
CN102026630A (zh) | 2011-04-20 |
ZA201007107B (en) | 2011-05-25 |
JP2011520818A (ja) | 2011-07-21 |
EP2273987A2 (fr) | 2011-01-19 |
AU2009248328B2 (en) | 2014-10-23 |
BRPI0907298B8 (pt) | 2021-05-25 |
AU2009248328C1 (en) | 2015-05-07 |
ES2426963T3 (es) | 2013-10-28 |
CA2724191A1 (fr) | 2009-11-19 |
DE102008023345B4 (de) | 2014-12-04 |
AU2009248328A1 (en) | 2009-11-19 |
AU2009248328B9 (en) | 2014-11-20 |
DE102008023345A1 (de) | 2009-11-19 |
BRPI0907298B1 (pt) | 2019-05-28 |
KR20110009700A (ko) | 2011-01-28 |
KR101588479B1 (ko) | 2016-01-25 |
US8758803B2 (en) | 2014-06-24 |
WO2009138170A3 (fr) | 2010-03-18 |
US20110064830A1 (en) | 2011-03-17 |
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